"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel

26:31But those are great types of logos to be early design partners because, one, they want to make sure they continue to stay on the cutting edge. But two is they are – to try and build something without that guidance is really, really, really hard because they're not using it. So you need that user feedback, and you also need to tie that to the executive value. Right. So it's actually a lot. It's very hard to do. But if you can come out of it and upsell a design partner to a full rollout customer, such huge. Such a huge win for the market, for you, for your team and also for your investors, because it's the hardest customer to actually truly convert.

27:23They've been it when it was messy. They usually got a low price point. But if you, again, frame it, say, listen, I would love for you to be a design partner. I want a little skin in the game to get you to put it. Here's where we want to go. And you'll get a discount because you were in the beginning, but I'm setting the framing. Here's where we want to go with pricing. Here's where we are today. You'll always have 30 % concession in perpetuity because you were there with us on day one. So again, it's not about, you know, asking for$10 ,000 and then not expecting that design partner to upsell and keep it flat because there's no growth there.

27:57It's a flat, you know, it's about getting that early design partner, set the framing, own the framing and let them know where you're going. Again,$100 ,000 to these large logos. If they want it, it's very easy for them to get it done. There's this really interesting underlying piece of advice of finding a company that pulls you in the direction that leads to success. A company that's kind of a visionary. There's the obvious companies that everyone's always trying to get these days, OpenAI and Anthropic and Stripe, I think, is one. Any advice for just picking the right early? What are signs that this is a company that will point you in the right direction?

28:34I think they have to be part of a logo that is deemed startup-friendly or in that world. And then I think it's the person. Right? Like, is this person excited to get feedback? Does this person buy in to where we're going? Do they see this world differently with like us? Do they buy? Are they in locks up with the founder vision? Are they excited to, to use a tool that's janky? Because it is janky in the beginning. But they know they know that where this can go can be incredible. So I think it's really about the person and making sure that they're aligned for what they're getting into. And I think a lot of people, I think a lot of salespeople oversell it.

29:21I think that's a common thing that happens, right? And that leads to churn. That leads to frustration. That leads to sometimes just canceling the contract. They oversell the initial kind of design partners phase of the product. Yeah, design partner, even full rollout. and it's so, so important to tell them, here's where we are today. Here's what we cannot do, which is just as important. It builds trust. Here's what we will allow you to do in the next six months. Do you want to be on this journey with us? And it's really ugly right now, right? Barely anything exists, but like we would love your voice to be a part of it.

29:55One of the biggest fears I think founders have is having a company pull, basically build just for their use case and then it ends up not being used by a lot of people. And so like how far do you go? fixing their specific problems? Any advice on just how far to go with one company? That is the founder's job. The founder's job is to have a clear vision and do not let anything delineate from that. It's important to take feedback in terms of what is the market's reality. But like it is the founder, and this is why being a founder so hard. It is the founder's job to interpret that because a lot of feedback you get is this is the old way.

30:33They're responding this way because it's the old way of working. They want you to build this because it's the old, that's how they're traditionally expecting to do that. It is not, here's where we're going. This is why we're not doing that. I hear you, but here's why we're not going to do that because we're going to completely change the way you do this. That is the founder's job. And I think, you know, we did a bunch of design partnerships, you know, late last year. And there was a lot of feedback given, a lot of feedback given. But the founder had such clarity with where he wanted to go that he was like 80 % noise, 20%.

31:15Had I not asked this question, like I wouldn't have gotten that gold in terms of where they are today. And like, it's that 80, 20 rule where 80 % of what they're going to tell you is probably going to be not related to where you want to go or based off of the old way. But that 20 % of like, oh, I did not think about it that way, that drives everything. Have you seen a design partner pull a company in the wrong direction, just kind of screw their path? Have you seen that? Or is that pretty rare? No, I don't think it's that rare because we hear people complain about it all the time. But I think it's more of an excuse.

31:49Coming back to this question of going after the enterprise enterprise versus SMBs. And again, early advice you gave is there's no, don't go in between. Either pick SMB small company, which I know you said there's a million ways to just to kind of differentiate what this means. But what I guess I think of employee numbers, like, you know, like under some number over a thousand is maybe enterprise. Is that like a good way to think about just like? Yeah, I mean, it depends. Are you selling per seats or are you selling, um you know based off of usage or are you selling off of like i think it also depends on the pricing model a little bit i i look at headcount too because it's just like it's just such an easy way to think about it because you can also gauge usage off that and a bunch of other things um but sometimes like the small companies like i think we're gonna see a lot more like a lot more larger companies become smaller because of ai not like significantly smaller but but also like high margins allow them to experiment more too.

32:50That's such an interesting point you're making there that like the way we designate enterprise versus SMB like may shift because number of employees may go down with AI. Yeah, oh yeah. So interesting. So where I was gonna go with this question is when people are deciding I'm gonna go enterprise versus I'm gonna sell to startups, like YC companies are the typical example they sell to their own YC batches. Any just broad advice of picking, okay, we go enterprise versus no, let's actually go startup. I think it's about, and I read this somewhere and I wholeheartedly agree with it because I've seen it live.

33:22I think it's about like, what game does the founder best understand? Are they like an incredible marketer and have some like competitive edge for how they can like win a massive audience? I would say go SMB and marketing led, or are they a bit more, you know, really understand how large corporations work and really excited to deliver on $100 ,000 plus type of opportunities or the value that they are building for is way more relatable to an enterprise versus a small business. That is really interesting. I've never heard of it described that way. I think about Linear, which started very startup-y.

34:05And my take is they did that because changing the way you work is really hard. And their bet was like, let's start with companies and grow with them. And over time, that becomes the default. Any reaction to that? I think that it sounds like that that's a great way to work because that's a technical tool, right? So that you need to have the right, you also need to have the right infrastructure to sell, right? Like I think Slack, I mean, look, Slack and the Microsoft teams are still battling it out at the enterprise. I think it's also like how you plug in and how you integrate. And do they even have the right systems to support you um the thing with open ai and and is like they didn't have to connect to anything uh say more about that so like the the value people were people were bringing their own use cases to it right and they don't it's not like they they well they can ingest and they built that it's a brand new thing and they started they started i think i i this is someone told me this, so this could be hearsay, but I believe that they were already speaking to CTOs even well before they released to help them explain where this is all going and get their buy in.

35:16And it's much easier to get into the enterprise when you're like, we won't even touch your data. Won't even touch your shit. Just use it to solve problems. And then we can build trust and then start to integrate and connect the pipes. But part of the challenges with selling in the enterprise. You're like, all right, well, let's connect all your consumer data. Whoa, that's extremely risky. So you have to start small and low risk, which is like, hey, what is the subset of consumers that churned? Let's figure out how we could have made them happier or whatever it be. So that data is lower risk. So again, it's also understanding your market and understanding what their ability to experiment is.

36:03It's interesting, this distinction between OpenAI right now and Anthropic. I don't know if you've been seeing kind of their growth. It feels like OpenAI is very consumer first, and Anthropic is more and more winning on B2B. I saw this chart recently where they're like overtaking OpenAI now on B2B. I don't know any reaction there of just like these two different approaches. I don't because most enterprises I'm talking to mention Gemini. Oh, interesting. Yeah, or Microsoft Copilot. So I don't hear much about Anthropic, to be honest. So that might be more of like a small business startup-y. I don't know.

36:41Or it's a different part of the organization that's using it. Yeah, that's a whole discussion or bundling right there of like Slack and Teams and then just, yeah, Gemini just kind of coming in automatically. People don't have to adopt anything new. Yeah, totally. There's something else that you talk about that I love that I don't think people talk much about, which is that enterprise sales is very creative. Oh, yes. Talk about that. So I personally believe that small business sales is really a, I used to think it was more science than art, right? It was more like, you know, figuring out what didn't work, running experiments, you know, testing and validating, which I do believe that's to get to like foundations, Like where do we play?

37:30What do we want to do? Like that early, early, early zero to one. From one to 10, I think it's more of an art, right? Which is how do I take my learning and how do I package it up where I own the framing? I can speak to very specific alpha. I can vision cast and where I better understand the problem over time better than the market does. and it's all about deal crafting. They just need to feel like the value they're getting out of it is way more than the cost. And it's sometimes about giving away things that don't really cost much to you, but are super expensive for them. For example, hey, we're selling X tool.

38:19We can build out why specifically for you over the next year and integrate it because I know that you would have spent X number of dollars on engineering resources or you wouldn't have gotten an engineering head internally to do this. But we're just going to leave it to you. You've got to give us a year to build it out. Again, you're not letting them sidetrack you too much. You're kind of containing it. We'll do that for you at no additional cost. That's huge value. Right? Or, hey, we're going to run an event and we want you at the forefront of it. We want you to be a speaker. Huge value, right?

38:56So it's like all of these additional things that add value beyond just the product, but are all part of the product and the vision, right? Everyone keeps thinking the product is just what goes into their hand. The product is pricing. The product is the opportunity, the framing, and not letting them compare you to something else. And I know we talked about on our first call, which is as soon as you become a comparison, as soon as you become one of three that they're testing out, you've already sort of lost. It's all about differentiation, right? And it's all about here's what you will be able to do tomorrow because of how we're going to serve you today.

39:39So along those lines, it reminds me in our first chat, you actually made this point that I've never heard anyone else make, which is that services are a really good way to start getting into companies that were most founders here like no don't just like don't do manual stuff for the company build a product that you can scale your advice is the opposite actually start with sell services talk about that enterprise is the number one thing they buy services that's they know how to do it it's super easy it's they they like they do it all of the time it's like the most consistent thing they do it's their largest budget item I don't know, right?

40:10External resources, consultants, whatever. If they have a very immature way of understanding the problem or they've never purchased technology to solve it to some extent, right? Either one, you are doing something that's never been done before, which is like, you know, rare in today's day and age, or they might just be like laggards on the journey. So you have to decide, is this someone you really want to be working with? And if so, selling them a service, even though the technology is powering it on the backend, is the fastest way to get your foot in the door. It's what they know how to buy. Now, the idea is that once you sell that service, once you get that foot in the door, then it's to guide them towards the product.

40:58Hey, you're spending so much here. Why don't we get you to come in and leverage the tool that's been powering this the whole time? and move this more into technology serving you versus the human. Wow. I think this will blow a lot of people's minds. Palantir. Palantir, this forward deployed engineer. That's exactly what they're doing. Right? Like, you know, there's a lot of companies that, like I'm sure, OpenAI. And this is what someone told me. They were in and talking to CTOs and helping them better understand how AI and their organization can better work together. And it was them coaching them and educating them, whether they did it for free or not, I don't know.

41:35but they got their foot in the door, they started to build trust, and then it gets adopted. This is the epitome of doing things that don't scale. That advice we always hear. This is like, okay, this is what that looks like. Like, we will solve this problem for you. We are using software to do it. And then over time, oh, you could just do this yourself. It'll cost you less. You can scale this. Yeah, that's right. And they don't even need to know at first that software is doing it. That could be the magic part, which is like, guys, we literally, we are literally doing this with our technology. Today's episode is brought to you by Coda.

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43:18coda.io slash Lenny. There's a lot of talk these days about this idea forward deployed engineers, something volunteer was really famous for just essentially an engineer sitting in your office solving problems with you like basically as an employee and then through that they learn what software to build is that something you're seeing too oh yeah i think you know i think that that um a lot of companies a lot sorry a lot of um folks that serve the enterprise they they have a they have a butt in a seat in their office like you look at these large consultancies like mckinsey they're not in their headquarters they're in their client's office all the time and the other interesting thing and proof of this is how many people go to a Deloitte or Accenture and expect them to be a channel partner?

44:02This is exactly what this is all about, which is they sell the service, they come in and then they introduce, hey, look at what this startup is doing over here. You might want to give them a shot. The problem with channel partnerships and why I don't believe in them is there are a hundred of you on this list, right? And you're expecting them to sell it on your behalf. Biggest no-no. They're not vision casters. They're not visionaries. They're consultants. But it goes all towards like, I remember startups saying, oh, I'm going to go win over Accenture and then have them disseminate me into their clients.

44:37And I'm like, as if that's a workable strategy. Okay. You know what might be helpful is let me try to summarize some of the best pieces of advice you've shared so far. And this is specifically for folks trying to go from about a million AR to about 10 million AR. And then I want to ask you just what's most different about those two stages, but let me share this first. So advice one is go for tier one logos earlier than you think you should, because they're early adopters. They can move fast. They can pull you in the right direction. And they excite investors too. Yeah, for sure. And other leads.

45:15And other talent, future employees. Yeah, exactly. So the counterintuitive insight here is you think they will move slow and be too busy, but they are actually the early adopters. That's right. They have to maintain that number one spot. And also all of the people that are in the number two, number three, number four spot all want to do what number one is doing. So it's also like pure referenceability, too. And the point about them being the early adopters, like the people that join the Stripes and OpenAI and Anthropics are like the like they individually love technology and love the latest stuff.

45:50So like as a human, they're like, oh, this is cool. That's exactly right. I'm just being with myself, aren't I? That's kind of funny. Yeah, that's a good saying. So two is ideally try to price closer to about 100K, like 75 to 150 ish K is what you said most enterprises are used to buying. So instead of starting or even sticking with 10K, 20K for too long, you need to make yourself go towards 75 to 150K. That's right. Yep. And if you were to sell a service, because I know we're talking about selling services first, prorate that over time. So maybe it's 10K a month. So they start to get used to what that pricing looks like.

46:28So this is a way to make it feel, this is like how you get to 75 to 150K is there's a service attached to it. It's not just, here's my SaaS product. Like that's we will solve this problem for you. Our person will be sitting there doing this for you. Yeah. Or it's a, no, it's a technology too. I mean, you can add the services. I always, well, let me take that back. The service, whether the services is bundled into it or not, that some people will unbundle it. Other people will say the services is a part of it. But yeah, it nets out to 75 to 150K. That's right. Okay. And you said that it's okay to start lower on ACVs and deals, but you need to push fast towards 100K over a few months.

47:05Yeah, that's right. If you can get into an enterprise for$10K in a month, which is not doable, but if you could, and you could go from$10K to$50K in four months through an expansion strategy, all game. That makes sense. But it's really rare and very hard to do. And so there's two different paths there. One is land cheap and grow quickly. The other is move your ACV average up quickly. That seems like both. The latter is probably the more common strategy is just keep increasing prices. Because the former, you can get tripped up because they could say, okay, now give me an economical price for doing this for 100 people.

47:42And then it all kind of evens out because now you're at the 100K deal anyway. But there's more room for error, which is why I say go in and try to land 100K. By the way, in our first chat, we talked a lot about the procurement process, which is what trips a lot of people up and is really painful. And I vividly remember that conversation still. So if people are having issues getting through the sales process and procurement, a lot of good advice there. And getting stuck in procurement is usually because you're not speaking to a senior enough person and they don't know how to navigate it, which is why I'm like that executive needs to be involved.

48:19Because as soon as the executive picks up a phone and tries to get a hold of like their buying group, things move. right like when people say oh i'm stuck in procurement i'm like oh that's a that could just be a qualification error and you never get out of it because you sold to someone too junior um so that's why the 100k is such a safe zone because even for 10k you might have to go through procurement so um this is like the surest way to make sure that like you don't um listen i've seen 10K take nine months to close. No bueno. Yeah. So. Okay. Next piece of advice is this idea of vision casting instead of problem solving.

49:00So the advice here is instead of here's your problem, here's how our product solves it is here's how you will achieve alpha in the market by adopting the software. We talked about the example of cursor where if you adopt cursor, you're going to draw the 10X engineers that are joining other companies right now. This will give you a big advantage. That's right. And yeah, it's pain versus opportunity, especially in the age of AI. And I know that we're moving into the next dimension. It's all about solving for a gap. It's seldom about solving for a very, very specific problem because people are trying to figure out what's our AI strategy?

49:36Where are we going to go with this? What is the world going to look like? I want to be a part of that new world. So it's a great time to be doing that. And then there's a bunch of advice we shared about design partners of just how to select them. Your advice is definitely have design partners because they will help you build the right thing. But as a founder, you need to have a clear vision and sense of where you want to go and not just build everything they're asking you to build. that's right because it's important to say no right like um and then and that's all part of the framing right which is like here's here's we want a little skin in the game like you set the price but here's where here's what we're marching towards in the next six to twelve months like are we aligned there if we prove if we deliver on what we say we're going to deliver are we aligned there and and do that kind of handshake is there anything else that i missed that you think is really important for this stage.

50:29So one to 10 is no longer the founder. Maybe the founder comes in in very strategic points, but you need a really good enterprise salespeople, right? Taking someone from small business and expecting them to do enterprise sales, big no-no, it's a different game, right? Vavily a different game. You need to understand how corporations buy. You need to understand how executives think. You need to better understand And simply just like what the enterprise business model is all about and like their ability to take on risk. People will bring in like super junior enterprise sales reps. And I'm like, you're looking to sell to an executive and you have this person that's five years out of school with no corporate experience doing it.

51:12Again, unless they have some extremely deep experience in the industry or are just a unicorn in terms of like, wow, this person can sell ice to an Eskimo kind of thing. A junior person converting an executive, again, the founders involved, maybe that's doable. But usually the founder can't be involved in every deal. And you need people that can, I always say you need people that can cosplay a founder, right? Which is like selling the vision, getting them excited, like running through a wall to get the deal done and getting creative on how. None of my deals look exactly the same. Every deal looks different.

52:00And that's okay because every organization has slightly different opportunities of where they want to go. And you have to kind of build towards that. And the framing may change. So it's this ability to like adapt from what you're hearing and like let that compound over time. But like I always say like can this person cosplay the founder? I think that that's the best type of salesperson because it doesn't feel like sales. It's more of the art. This is amazing advice. What is a common profile that you've seen be successful? Like what level of seniority, what kind of personality, any traits to look for?

52:38Maybe a former founder, if you can get that. Because they're used to selling, right? They've sold investors and they've sold employees. Two is someone with no sales experience, but has deep product experience or an engineer and can like think about things in a unique way where you can where the market's like, oh, this is so interesting. Taking a typical salesperson and putting them into a sales role almost always is where people get frustrated. The market, it feels salesy. Like the market doesn't want to be sold to. They want to buy. And I know that this is like, it's very hard to hire a really good enterprise salesperson, right?

53:21I mean, the number of people that I've interviewed, I can count on my hand the ones that I get really, really excited by. It's almost like, you know, coming across a great founder, right? It's like, you know, it's not as common as everyone expects. And I think that that's true for engineering. I think that that's true for sales. And I think a lot of people, sales is like, oh, just throw a body into it. The product will do the work. Advice I often hear is don't hire a kind of a senior VP of salesperson from a bigger company. Yeah. Do you agree with that? How, what's like two senior? So the bigger company thing, the brand was doing all of the work.

54:01The brand built the trust. You need this person to be able to build the trust. And like, they're usually, the product is still so new. The product is the founder in the zero to one stage. The product is just starting to get like a case study. You probably have maybe a few references, but it's still very, very early days. You need the market to believe the salesperson and you need that market to know that they're trustworthy. A VP of sales at a large company, I would say they're best suited for a large company because one to 10, you're running through walls, right? You have to figure out, you know, you're doing a lot of convincing.

54:36You're doing a lot of educating. You're doing a lot of creative deal crafting, a lot of owning the frame. It's not necessarily selling a product. It's selling that future value, which a VP of sales at a large company, it's a very different. It's a different game. It's kind of like the SMB and enterprise. It's interesting you said when you described the profile of a great hire here is you said they don't need to have done sales. If they have done sales, what's like a number of years or kind of like what do you look for that tells you, OK, this is a good fit for the first hire? I actually think it's less about experience and more about the person.

55:09Like, does this person make you feel good? Do you want to buy from this person? I think Jason Lemkin said that best. Like, would you want to buy from this person? Can they sell you a pen? The classic. Yeah, exactly. You know, do they mimic or mirror the market they're selling to, right? It's much easier to buy from someone that looks and feels like you than it does from somebody that's like, you know, in a totally different realm. And also like an executive wants to talk to another senior person, right? They don't want to talk to someone that just graduated from college and is selling them the new way of working.

55:45Like, what do they know? So I think it's tricky. I would say like, you know, someone with no sales experience makes it feel different and special. That's what I like about it. Someone with sales experience knows how to navigate and probably qualify better. But it's almost like the blend of those two things. And that's why I go back to like cosplaying the founder, which is like, could this person, you know, could this person like close a future employee? Right. Like, do they get excited about the problems they're solving internally and the vision that they get to sell to? This actually was a reader question, a listener question from Twitter.

56:24So Peter Dedenne asked, how do you how do you make this first salesperson as enthusiastic about the product as you? Is there something you can do? Is it more just they already are and you just leverage that? Incentives. Sales people love to make money. So if they know it's possible, if they know it's possible, you'll be shocked what people can get done. If they see how much they could make. Amazing. Right. I imagine there still also has to be an innate excitement about the product. They have to believe in it. They have to believe in the founder. but like incentives usually make the world go round.

57:04But yeah, is this person, are they asking the right questions to the founder? Are they, you know, I always, the best thing to do is have the founder join the first five calls. You know, after five calls, if this person has what it takes and don't be afraid to fight, like one in every two salespeople usually are fired. It's a very, yeah, it's like, Like it's a very high failure rate. Because you can tell pretty quickly how it's going. You can tell or the vision of the founders is just very wrong. Speaking of incentives, do you have any quick advice on how to structure their comp? Just like how much they earn?

57:45It's usually 50-50. So it's 50 % OTE, 50%. So it's a 50 % base salary, 50 % OTE. And then how much of the sale do they typically get? Say the first sale is higher. It depends on the price, the size of the deal. But in technology, it could be anywhere between like 8 % and 12%. So rounds out around 10%. Okay. Awesome. When do you hire the first salesperson? Is it around the 1 million ARR mark usually? Yeah, it's around that 1 million AR mark. And it's usually when you have your first 7 to 10 customers and there's some pattern recognition around it that you can share with somebody else. There's some consistencies.

58:31Otherwise, it's just like, that would be very hard. Basically, as a founder, you have to figure out how to sell enough times so that you can show someone, here's what's working. And this is the common thing I hear. Well, I'm a$10 million business. I'm like in this small business space, you're$0 in enterprise. It's a zero to one right now in enterprise. It's a totally different game. It's a different value proposition. It's a different deal structuring. It's a different target market. It's a different risk tolerance. It's totally different. So don't be blindsided when it doesn't work. There's a lot of unlearning that needs to happen when you move into a new market.

59:12So the advice here is make yourself sell up until around a million RR, especially if you're trying to go enterprise selling to enterprises yourself as a founder, which is really hard. You have so much to do and you have to be selling this thing for a long time. Yep. And then, you know, try and find someone that like you get excited by. Like, it's funny. If you ask the founder, are you excited by your salesperson? I'm curious what the real answer is. It's like, well, it's a butt and a seat and it was hard to hire. So interesting. I remember I think it was Jason's advice was to hire two people immediately.

59:45Right. So you can compare them. Do you agree with that? Yeah, because of the 50 % failure rate. I think that's exactly right. So, yeah, even a taller order, go find two people that are good. But, yeah, I think that that's right because, you know, one in two will fail. Okay. Let me ask you another reader question from Hang Huang. This is kind of in a different direction. So he says the biggest challenge is always cutting through the noise to get that initial meeting with the right decision maker. How do you even get their attention? It's the vision. What is the opportunity that you're selling? That if they are excited by that, they will take a call.

1:00:25I see it all the time. And don't give away the farm. Keep it to three sentences. And I know I said this on our first call, but say something counterintuitive. Make it feel different. make it feel like they can learn from you by taking a 15 minute call. Right. You know, you see the standards of like, oh, I came across your LinkedIn and, you know, are you looking to grow your business by 15 percent? It's like, what kind of statement is that? And this is in the in the cold email they get. This pitch. Awesome. So this is a good segue to another reader question from Hugo Alves, co-founder of Synthetic Users.

1:01:03He asked, what's the best advice for going from healthy inbound to targeted outbound? Healthy inbound usually is a marketing-led initiative. So that's a marketing game. It depends like what deal value you're selling. Are you selling a$5 ,000 deal? It's got to be marketing-led to make the engine work. If you're selling a$100 ,000 deal, you're doing outbound day one. So again, it breaks it into those. This is like that blending of the, I see a blending of that question. This is where you're doing small business, you know, marketing led activities or are you a sales led organization selling a hundred thousand dollar deal?

1:01:39And the reason this important, just in case it's not obvious, is you're not going to make money if you're selling. People are spending time closing deals that are making 10, 20K. Just the ROI on that won't work for your business model. That's right. Yep. Awesome. By the way, let me just say, Jen, this is this is like an incredible conversation already. We've gone through so much. This is like exactly what I was hoping to get through. We've gone through so much advice that I think is going to be so helpful to so many people. There's a few things that your partner, Justin, also suggested I ask you about that I want to touch on.

1:02:13One is you have this question that you ask founders a lot that opens up their mind. You ask them, if you give your product away for free, would people even use this? And every founder is like, of course. and then you ask a customer this and they're like, nah, we wouldn't use this. And that just blows their mind. Talk about just the power of that and how you recommend people approach this. I always say, ask the questions you're afraid to because that truth is gonna get you closer and closer to the answer. So I'll ask a client straight up on a call. I'll say, honestly, do we think we're gonna get the deal done this year?

1:02:46Like, is it possible? They'll give you the real answer. Like, and people are afraid to ask. But like the other side is sort of, you know, if they're in it with you, they don't care about that question. Right. Can't ask that question on day one. But like if you are and we didn't talk about this, but maybe this is important. Every single enterprise deal I have done. The deal is done. The deal is closed and pretty much done through text. It's not on email anymore. Or it is a relationship you're building with someone where if my enterprise client called me, I'm picking up that phone immediately or I'm responding them to immediately because that builds so much trust.

1:03:31If they know they can call on you, they're going to get you to pick up and they know that you're going to do everything humanly possible to make sure that this is successful. People will turn over rocks for you. like I have a client at a fortune 10 company where I was like it's so important we get the deal done this year like is that possible and she's like it's a tall order but like if it's going to help you let's do it like these are how enterprise deals gets done it's relationships and it's it's this like and this is why I'm saying like structuring the deal make it feel like you went to bat for them and in often often cases you are going to bat for them and structure it in a way that makes sense for them.

1:04:16Everyone kind of just tries and pigeonhole. Pigeonholing and deal structuring consistency is important for a$10 ,000, sub$10 ,000 deal. A$100 ,000 deal, it very commonly will look different every time. April Dunford was on the podcast and she shared this really interesting insight that the reason people behave this way is the person at the company buying this thing, their ass is on the line also. So like their reputation is on the line for this thing to work out. So they want it to go really well. That's right. Again, it's that they do this one in every three years, one in every two years, maybe one in every five years.

1:04:52Hell, I don't know. It is not at all. They don't do this every year. It's very rare. It's no one likes a new tool. No one. Not you, not me, unless it changes everything. Yeah. Figma is a great example. That slack. Everything you've touched. everything that worked out you said that you ask these questions that people are afraid to ask what are some other examples of questions you often ask that people are afraid to ask i will say listen this this is 150 000 engagement i will co-author it with you where we can make this a little bit bigger if you need something else we can make it a little bit smaller in year one but in year two it steps up.

1:05:36How do we get this done so when you go to bat, it's a win? They seldom, seldom do they take it to the wrong side and try and discount you. I've actually never seen that because at that point you have a relationship. So co-authoring the pricing is so important because they need to know that they go to bat, they can say, I got this out of them if we get this deal done. Right. So this is why, like, when I say every deal looks the same, you're asking great questions because it's explaining kind of why I meant by that. But like, this is another example of like why every deal in the enterprise sort of looks somewhat different, because a lot of it is co-authored.

1:06:19So, again, if someone wants a slightly lower price, give it to them, but maybe they'll lock them in a little bit longer. There's another point that Justin makes that you've touched on a bit, but it's when you hear no. The way he phrased it is Jen always talks about how no is the best answer to guess. Because no is data that you can use. Talk about that. I am a qualification crazy person. I will not get in on another call with someone because on the first call, it's either a yes or no. There's no in between. Like it is people, humans are like we're so different and we're so unpredictable. We're also so predictable at the same time, right?

1:06:57Like it's very obvious if someone is excited and wants to do something. It is so obvious when someone is just trying to be nice. So I will say to them on that call, like, I'm sort of getting the vibe that this might not be a good fit or might not be good timing. Like, did I misinterpret that? And they will usually say, yeah, you're right. It's probably not a good. And then immediate. Great. I would love to stay in touch. You've just saved a relationship and you just gave yourself a ton of time. And the implication here is just to your point, you're limited on time. You don't want to be spending time going down or rival level and get you anywhere.

1:07:30Yeah, exactly. I'm going to take a quick tangent on tools. What's kind of like the state of the art on go-to-market outbound tooling? I don't use a tool because I believe in the manual. Okay, and I'll explain why. Every single note I send is slightly different because I see a picture of them and I'm like, oh, I don't know if that's going to land. I'm like, oh, they actually might appreciate this. It's weird. Like visual cues are so helpful. A picture is a visual cue. You know, looking at how long they've been in the role, looking how long they've been at the company. I use all of these little things and I don't, I seldom customize a note in a way that like people expect, which is like that first like customized sentence because AI does that and everyone's doing that.

1:08:19So I go the opposite stream, which is like remove it. And I customize it with how I frame it or the subject line. Yeah. So it's like if I'm talking to someone like a peer, I might say like, quick question, like QQ. If I'm talking to someone that has a bit more experienced, I might write a little bit of a tighter note, not all lowercase. So it just depends on who you're speaking to. And again, this is why it's okay to spend a little bit of time on this because it's$100 ,000. It's actually a million dollars at the end of the day because a$100 ,000 deal, if you play your cards right, turns into a million dollar deal over three to five years.

1:09:02I love how much you enjoy this. It's so fun to hear. So essentially, what are you doing? You're sitting on LinkedIn finding folks to ping and then you cold email them individually, manually. It's so weird, Lenny. Like I have no process. I kind of just go with like the vibe. Like I'll read an article about Tesla and I'm like, huh, they could be interested in this. Not because that article had anything to do with the problem I'm solving, but because I'm like, this feels like a good Tesla day. Like it's like it's hard to describe. Like it's a very emotional thing for me. and, you know, not to toot my own horn, obviously, but like I've been successful in sales and the most successful salespeople can't explain why they're good at it.

1:09:51It just comes to them naturally. It's just like an emotional thing. It's like the world's best founders, how do you be a good founder? It's very, very hard to define. How will you become a good engineer? Very, very hard to define. So, like, I don't believe in I don't believe in like playbooks. I don't I like I believe that like there's like a feel to it. Like I emailed like the chief legal officer at a hedge fund once and he responded to me because I wrote to him on Saturday. I knew it was going to be busy. I made it one sentence and it was like tweaked for him. Do you feel like this is going to be the way as AI, as DRs just kind of take over and everyone's getting billions of emails that feel AI-ish?

1:10:37Yes. So I guess maybe speak more there. Just like is the alpha essentially just become human, don't automate? Yeah. And the thing about AI tools is they're all pulling from the same databases. So I'm like, I want to email someone not in the database that's getting hit by a million folks. I want to take a back door in, not the front door where everyone else is trick or treating, you know? And this is effective for a very large deal, which is what you need to be doing anyway, because it takes a lot of time to do it this way. Yeah. Interesting. So you're not like sitting in clay. You're not like Apollo.

1:11:16I don't know all those tools. You're just like finding people yourself. Yeah. Do you start with a target prospect list, at least? Just like, here's the companies that are the perfect fit for this and let's work through them. It's all in my brain. because I've been doing this for so long. I like I have in my brain. I'm like, these are my early adopters. These are I'm going to go to after I close those logos because they get excited by those logos. So it's just like experience of like, you know, you land. I don't know. You you land a Walmart. You're going to go to, you know, the rest of the industry and say, hey, we're working with Walmart, you know, versus like you go to, you know, some, you know, lower end enterprise company and they're like wait what do you do what like i can't even comprehend like they're also the most strategic people some of the most strategic executives are at these tier one logos that's why they're tier one because they've got like super smart like really capable folks they also extract the best talent the best talent likes to experiment and continue to improve so it's like it's this constant it's like this compounding thing For someone that isn't Jen and has all this experience, say like their founder, their head of a million ARR, they're just like, okay, where do we find our customers?

1:12:27Do you have any advice for coming up with a – just kind of coming up with who we should go after? Should they be using these tools? Should they be hiring someone like a Jen? Like I know this is what you do for companies. So, you know, one proud is go hire Jellyfish to help them through this. The founder. The founder. I would say the founder – this is sort of in tune with them in a way. they just have to like find it they like it's all it's so weird to say it's all vat and i hate saying it because it's like it's like a commonplace thing to say but it's like there's this thing about like flow and it's like some of these brands are in flow with you right now right like um you you you you you found this insight from somewhere who else what's the next adjacent ring of people that like would buy into that and so what i'm hearing is just like pay attention to what's happening what companies are yeah in the news what companies are doing interesting things what are the kind of the early adopters in the market if it was just a database list and it was just about figuring out the right messaging and then you know emailing folks we would have known by that by now that's so interesting okay maybe one One more question.

1:13:41This again is from Justin. He shares that when you hit resistance, you never argue, you reframe. If someone says we already have X solution, you'll agree and pivot and totally X is great for this thing, but here's what we can do. This is why it's sell to the alpha. Hey, I know I listen, that problem you just described, you're right. You have a tool for that. We're taking you much further upstream with value. This is the opportunity I want you guys to have access to. I love it. Jen, I've gone through everything I was hoping to get through. On the other hand, I feel like we could do another hour on all these things.

1:14:16I feel like we need to do three in. Yeah, we need around three on the next phase and all the things that people want to dig further into. Before we get to our very exciting lightning round, is there anything else that you wanted to touch on or share? This stuff is really hard. It's very hard. Like sales is also all about like learning very, very quickly from the rejection. The rejection is good because it's a forced learning and you never want to go through that again. But you have to be, I don't like to use the word cringe. Like you, you can't be afraid to cringe is like, you know, bringing your AI recorder into a call.

1:14:56Like that's cringy. But like sending 15 notes to people that you can deliver serious value to, like, don't be afraid. And don't be afraid to, like, ask the hard questions. Be different. The whole game is about, oh, this feels different. That's what people want access to. And yet everyone commoditizes themselves. Like, they try and mimic whatever, you know, they try and mimic, you know, a forward deployed engineer, just rename it. You don't have to use the same nomenclature. Everyone gets excited by the new because the new could be the next thing, the thing that changes it all. So that's why I'm always like, don't be better, be different.

1:15:40An amazing way to end it. With that, Jen, we've reached our very exciting lightning round. I've got five questions for you. Are you ready? Yeah. First question, what are two or three books that you find yourself recommending most to other people? I do Twitter accounts. Oh, Twitter accounts to follow. Oh, yeah. Okay. Like Lenny, the day I have time to read a book. Period. Period. I would love to be reading books. Cool. Twitter accounts to follow. Yeah. Obviously you, like you produce some of the best content, truthfully. Appreciate it. Like you get into the minds of people that like, they're not even giving this insight on Twitter.

1:16:25Who else do I absolutely love? Jason Lemkin. So for sales, Jason Lemkin is awesome. Awesome follow for sales. And also he had a great, great recording with you. So link to that because that was a great piece. I actually learned a ton from it. I love Gavin Baker. super nuanced takes like takes a lot of like obvious statements but like shares a lot of the non-obvious uh insight he's great uh jason cohen have you ever had jason cohen on the cast jason cohen a smart bear jason yeah yeah yeah he's coming on the podcast and at the end of the year oh that's awesome what a great plug for him right there um yeah those three would be great I know they're all men, but...

1:17:11Great tips. Yeah. Next question. Is there a favorite recent movie or TV show that you've really enjoyed? I know you said you have time to read. This is going to be embarrassing. Baywatch. Baywatch? Yeah. I'm watching Baywatch channel. It's just so nummy. And it's like 90s classic. Baywatch. Wow. I've never heard that one before. So this is original Baywatch. This is original Hasselhoff, David Hasselhoff. Yeah, Pamela Anderson. Pamela Anderson, the original cast. Amazing. Yeah. Okay, deep cut. Is there a product you recently discovered that you really love? So the number one thing for me right now is an app called Playground, which is the pictures of my toddler that they upload into the preschool so I can get the daily updates on what's going on in preschool when he's not home.

1:18:03Amazing. I need that. We get emails and Google photos. I would really love that. Yeah, there was another one called Class Dojo. There's a few of them, but Playground's the one that this preschool's on. I love Class Dojo. I'm a small investor. Are you really? I am. Oh, that's awesome. How about that? Two more questions. Do you have a favorite life motto that you find yourself coming back to find useful in work or in life? Yeah, be direct. Like, cut the fluff. Like, give me the one cent. Give me the bullet, not the paragraph. Final question. I was told that by Justin that you've never read a sales book.

1:18:38You've just learned to do this. If you were to read a sales book, if there was someone else out there that you look up to, you learn from, is there anyone else out there in the world of sales that you most respect? I think Jason Lemkin has the strongest understanding of sales. His content is unbelievable. He speaks about it clearly and cleanly. I would say, and as I mentioned, unbelievable Twitter follow. I'm a big fan of his. I've actually learned a lot from him too. Like the 50-50 thing or a higher to salespeople, he's spot on. Failure rate's actually probably higher than 50%. I love that guy.

1:19:16And he's so like AI forward these days. He's just building. He almost took down Replit with his complaints. It was a whole new cycle. And he's super direct. Like sometimes he says things that are like harsh, but you're like, he's not wrong. Love it. I got to get him back on the podcast. Yeah. Jen, this was incredible. This was everything I wanted it to be. I feel like we just leveled up all the founders that have listened to this in their ability to close. We're going to just create all the economic value and a lot of happy VCs from all the sales that will be closed as a result of the advice you shared.

1:19:48Two final questions. Where can folks find you if they want to either work with you or follow you online? And how can listeners be useful to you? Twitter. Every new learning or mishap I put right on Twitter. So it's like my personal diary. and super responsive on Twitter DM. What's your Twitter handle? Twitter handle. It's double J, so J-J-E-N underscore A-B-E-L. You did not make that easy for people to find you. Yeah, no, I know. I know, I didn't. And the J's from Jellyfish, is that where the extra J's for? Yeah, the double J's. And then also, well, someone else had the handle. So I was like, I need my name.

1:20:27By the way, just tell people what Jellyfish is in case that might be helpful to them. Yeah, so it's a consultancy that helps folks in the zero to one stage. And now I'm at general manager of enterprise at state affairs, which is basically giving citizens and corporations an inside peek into like what's actually going on inside the state capitol building. State policy has way more impact on you than federal policy. Federal policy is written more about. Incredible. I've only recently learned that that's what you're doing these days, and that is super impactful and important. So thank you for your work there.

1:21:02Stephen, democracy. No big deal. Jen, thank you so much for being here. Thank you so much, Lani. This was a blast. Bye, everyone.

1:21:24the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.